CAS 2086-83-1|berberine|16,17-dimethoxy-5,7-dioxa-13$l^{5}-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,13,15,17,19-octaen-13-ylium|Berberine|BERBERINE, ACETONE ADDUCT|16,...

General Information

Structure

Molecular Formula

C₂₀H₁₈NO₄+

Molecular Mass

336.36122

Exact Mass

336.12358306

Charge

InChI

InChI=1S/C20H18NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1

InChIKey

YBHILYKTIRIUTE-UHFFFAOYSA-N

Canonic Smiles

COc1c(OC)ccc2c1c[n+]1CCc3c(-c1c2)cc1c(c3)OCO1

Isomeric Smiles

COc1ccc2cc3c4cc5c(OCO5)cc4CC[n+]3cc2c1OC

Calculated Properties

JChem

LogD (pH = 7.4)

-1.28

LogD (pH = 5.5)

-1.28

Log P

-1.28

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

13.46

Polar Surface Area

40.80

Polarizability

36.92

Molar Refractivity

93.52

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

IUPAC Traditional name

berberine 16,17-dimethoxy-5,7-dioxa-13lambda5-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2(10),3,8,13,15,17,19-octaen-13-ylium

IUPAC name

16,17-dimethoxy-5,7-dioxa-13$l^{5}-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,13,15,17,19-octaen-13-ylium 16,17-dimethoxy-5,7-dioxa-13λ⁵-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium 16,17-dimethoxy-5,7-dioxa-13λ⁵-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2(10),3,8,13,15,17,19-octaen-13-ylium

Synonyms

BerberineBERBERINE, ACETONE ADDUCTumbellatine5,6-dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinoliziniumBerberineberberineBerberinBERBERINEberberineUmbellatine9,10-dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetradehydroberbiniumBerberine7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-[methylenebis(oxy)]berbinium5,6-dihydro-9,10-dimethoxy-1,3-benzodioxolo[5,6-a]benzo[g]quinolizinium

Names and Identifiers

Registration numbers

DrugBank ID

DB04115

Unique Ingredient Identifier

0I8Y3P32UF

CHEMBL

12089CHEMBL295124

PubChem CID

2353

CHEBI ID

16118CHEBI:41098CHEBI:22753CHEBI:16118CHEBI:3066CHEBI:13893

CAS Number

2086-83-1

Wikipedia Title

Berberine

Chemspider ID

22632,263

PubChem SID

465060511609671758145003

UniProt Database

B1NF19A2A1A0P30986P93479Q67A25Q7WTR3A2A1A1P45272Q948Y1P21820

BindingDB Database

50203126

MetaCyc Database

BERBERINE

Rhea Database

RHEA:23564RHEA:21268RHEA:13489

Patent number

EP1574218WO2006032380WO2007130777US2007197648EP1905436US2005257295WO2007090289WO2007113748EP0813872US2007190187EP0813871

FooDB Database

FDB023165

Protein Data Bank

3d6y7n7d7a3y1jum3np67c342qvd7n7e3bti6jwd4dbk3r6r5y0v7msv3vw2

NMRShiftDB Database

Beilstein Number

HMDB Database

LINCS Database

MetaboLights Database

MTBLS1033MTBLS630MTBLS2974MTBLS1191MTBLS742MTBLS2145MTBLS379

KNApSAcK Database

C00001819

KEGG ID

C00757

IntEnz Database

EC 1.5.1.31EC 1.21.3.2EC 1.3.3.8

SureChEMBL Database

Pesticides Database

ACToR Database

CompTox Database

PDBeChem Database

Registration numbers

Properties

Product Information

Certificate of Analysis

Download link

Safety Information

MSDS Link

Download link

Physical Property

Apperance

yellow solid

Yellow powder

Solubility

slowly soluble in water

Melting Point

145°C

Properties

Related Proteins

Related Proteins

Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB04115

Drug Groups

experimental

Description

An alkaloid from Hydrastis canadensis L., Berberidaceae. It is also found in many other plants. It is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal. [PubChem]

MP Biomedicals

05209343

MP Biomedicals Rare Chemical collection

Wikipedia

Berberine

Molecule Details

References

PubChem Literature

No Data Available

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References

Bioactivity